All Photos(1)

532657

Sigma-Aldrich

(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol

98%

Synonym(s):
Totarol
Empirical Formula (Hill Notation):
C20H30O
CAS Number:
Molecular Weight:
286.45
MDL number:
PubChem Substance ID:

assay

98%

optical activity

[α]20/D +41°, c = 1 in chloroform

mp

128-132 °C (lit.)

SMILES string

CC(C)c1c(O)ccc2c1CC[C@H]3C(C)(C)CCC[C@]23C

InChI

1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,20+/m0/s1

InChI key

ZRVDANDJSTYELM-FXAWDEMLSA-N

Certificate of Analysis

Certificate of Origin

G B Evans et al.
Bioorganic & medicinal chemistry, 8(7), 1653-1662 (2000-09-08)
Alterations of the C-12 and C-13 aromatic ring substituents of totarol (1) afforded the series of derivatives 2-14, and introduction of substituents at C-12 gave exclusively 2a-14a. The majority of these analogues were tested in vitro against the following organisms:...
Cailean Clarkson et al.
Bioorganic & medicinal chemistry, 11(20), 4417-4422 (2003-09-18)
The previously unknown antiplasmodial activity of the plant derived natural product totarol is reported. Novel beta-amino alcohol derivatives based on this natural product were designed, synthesised and evaluated for in vitro antiplasmodial activity and cytotoxicity. These derivatives showed antiplasmodial IC50...
Michelle B Kim et al.
Organic letters, 12(15), 3324-3327 (2010-07-06)
An efficient, convergent synthesis of totarol by a diastereoselective epoxide/alkene/arene bicyclization is described. The reported synthesis enables the preparation of related diterpenes totaradiol and totarolone as well as previously unavailable derivatives that exhibit comparable inhibition of the bacterial cell division...
M Dufour et al.
International journal of food microbiology, 85(3), 249-258 (2003-07-25)
Despite numerous papers being published on the use of hurdle technology to control food-borne pathogens or spoilage organisms, there is no commonly accepted methodology to quantify the level of synergistic activity. This paper describes a method to quantify in vitro...
G B Evans et al.
Bioorganic & medicinal chemistry, 7(9), 1953-1964 (1999-10-26)
A series of analogues of, and potential pro-drugs derived from, the potent antibacterial diterpene totarol (1) were synthesized in order to elucidate the minimum structural requirements for antibacterial activity and to seek compounds with good bioavailability in vivo. These analogues...

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